Abstract
The terpene 2-methylisoborneol (MIB), a major cause of off-flavor in farm-raised catfish and drinking water, is transformed by various different terpene-degrading bacteria. Two of these, the R-limonene-degrading strains Pseudomonas sp. 19-rlim and Sphingomonas sp. BIR2-rlima, dehydrated MIB with the formation of odorless metabolites 2-methylenebornane and 4-methylcamphene. These metabolites which have a structural resemblance to camphor, could be further transformed by camphor-degrading bacteria to more oxidized products. The bacterial dehydrations demonstrated here may have application in removing MIB where it is a problem.
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Altschul SF, Gish W, Miller W, Meyers EW, Lipman DJ (1990) Basic local alignment search tool. J Mol Biol 215:403–410
Birladeanu L (2000) The story of the Wagner–Meerwein rearrangement. J Chem Ed 77:858–863
Duetz WA, Bouwmeester H, van Beilen JB, Witholt B (2003) Biotransformation of limonene by bacteria, fungi, yeasts, and plants. Appl Microbiol Biotechnol 61:269–277
Eaton RW (2001) Plasmid-encoded phthalate catabolic pathway in Arthrobacter keyseri 12B. J Bacteriol 183:3689–3702
Eaton RW, Sandusky P (2009) Biotransformations of 2-methylisoborneol by camphor-degrading bacteria. Appl Environ Microbiol 75:583–588
Engle CE, Pounds GL, van der Ploeg M (1995) The cost of off-flavor. J World Aquac Soc 26:297–306
Finato B, Lorenzi R, Pelosi P (1992) Synthesis of new earthy odorants. J Agric Food Chem 40:857–859
Gunsalus IP, Marshall VP (1971) Monoterpene dissimilation: chemical and genetic models. Crit Rev Microbiol 1:291–310
IUPAC (1979) Section A-74. Bicyclic Terpenes. IUPAC Commission on Nomenclature of Organic Chemistry. Sections A, B, C, D, E, F, and H. Pergamon Press, Oxford. www.acdlabs.com/iupac/nomenclature/
Jüttner F, Watson SB (2007) Biochemical and ecological control of geosmin and 2-methylisoborneol in source waters. Appl Environ Microbiol 73:4395–4406
March J (1992) Advanced organic chemistry, 4th edn. Wiley, New York, pp 1068–1072
Martin JF, Bennett LW, Graham WH (1988a) Off-flavor in the channel catfish (Ictalurus punctatus) due to 2-methylisoborneol and its dehydration products. Wat Sci Technol 20:99–105
Martin JF, Fisher TH, Bennett LW (1988b) Musty odor in chronically off-flavored channel catfish: isolation of 2-methylenebornane and 2-methyl-2-bornene. J Agric Food Chem 36:1257–1260
Mills OE, Chung S-Y, Johnsen PB (1993) Dehydration products of 2-methylisoborneol are not responsible for off-flavor in the channel catfish. J Agric Food Chem 41:1690–1692
Napolitano E, Giovani E, Ceccarelli N, Pelosi P (1996) Tertiary alcohols with earthy odor. J Agric Food Chem 44:2806–2809
Schumann R, Pendelton P (1997) Dehydration products of 2-methylisoborneol. Wat Res 31:1243–1246
Sumitomo H (1992) Biodegradation of 2-methylisoborneol by gravel sand filtration. Wat Sci Technol 25:191–198
Tanaka A, Oritani T, Uehara F, Saito A, Kishita H, Niizeki Y, Yokota H, Fuchigami K (1996) Biodegradation of a musty odour component, 2-methylisoborneol. Water Res 30:759–761
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Eaton, R.W. Dehydration of the off-flavor chemical 2-methylisoborneol by the R-limonene-degrading bacteria Pseudomonas sp. strain 19-rlim and Sphingomonas sp. strain BIR2-rlima. Biodegradation 23, 253–261 (2012). https://doi.org/10.1007/s10532-011-9504-y
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DOI: https://doi.org/10.1007/s10532-011-9504-y